Man from Dating Site Brought His Parents on Our First Date with Their Ridiculous Demand – I Decided to Outplay Them

Who brings their parents to a first date? My boyfriend from a dating app did. But what really got me was the list of OUTRAGEOUS DEMANDS his parents brought with them. I knew I’d have to outwit them… but on my own terms.

When I virtually met Jacob on a dating site several months ago, we hit it off instantly. The connection felt real — the kind that makes your heart skip a beat when you see a new message notification. I grew to think that he was “the one,” but then when we actually met… well, let’s just say reality has a way of shattering our perfectly crafted illusions.

A woman holding a phone | Source: Unsplash

A woman holding a phone | Source: Unsplash

Three months of late-night texts and hour-long video calls had built up to this moment. Jacob wasn’t just another match; he was different.

While most guys led with cheesy pickup lines or bland “hey” messages, he had caught my attention with a detailed comment about my profile photo taken at Comic-Con.

“Is that a handmade Scarlet Witch costume?” he’d written. “The detail work is incredible!”

From there, our conversations flowed naturally. He listened, really listened, when I talked about my work as a graphic designer and my dreams of starting my own studio.

A woman using a computer | Source: Midjourney

A woman using a computer | Source: Midjourney

He shared my love for true crime podcasts and could quote every episode of my favorite shows by heart. When I mentioned my sister’s battle with depression, he opened up about his own experiences with anxiety.

“I feel like I can tell you anything,” he’d said during one of our video calls, his warm brown eyes crinkling at the corners. “I’ve never connected with someone like this before.”

“Me neither,” I’d admitted, feeling my cheeks flush. “Sometimes I worry this is too good to be true.”

He’d laughed then, running a hand through his dark hair. “I can’t wait to finally meet you in person. Friday at Coffee Beanz? 7 p.m.?”

A man using a laptop | Source: Pexels

A man using a laptop | Source: Pexels

“It’s a date! Finally!” I’d chirped, unable to contain my excitement.

“See you on Friday!” He said as I hung up, blushing.

I spent the entire week planning my outfit, finally settling on a gorgeous dress that my best friend Sarah insisted brought out my eyes.

“He won’t know what hit him,” she’d said, helping me style my hair.

Friday evening found me standing outside Coffee Beanz, smoothing down my dress for the hundredth time. Through the window, I could see couples enjoying their meals, soft candlelight flickering across their faces.

People in a cafe | Source: Unsplash

People in a cafe | Source: Unsplash

My hands were shaking slightly as I pushed open the heavy wooden door, the warm aroma of garlic and fresh bread enveloping me. My eyes nervously darted around in search of Jacob.

“Lia! Over here!”

I turned toward Jacob’s familiar voice, my practiced smile freezing on my face. There he sat, but not ALONE.

An older couple sat beside him, their faces beaming with smiles. My heart, which had been filled with excitement all day, sank to my stomach.

“Hey… um, hi, what’s going on?” I managed, my brain struggling to process the scene before me.

A shocked woman | Source: Pexels

A shocked woman | Source: Pexels

Jacob stood up, his bright smile unchanged as if this was completely normal. “Lia, I’m so excited to finally meet you! These are my parents, Linda and Patrick!”

Linda, a petite woman with perfectly coiffed gray hair and gold earrings that probably cost more than my monthly rent, gave me a practiced smile that didn’t reach her eyes. Patrick, sporting a dress shirt that seemed a size too small for his frame, barely looked up from his menu.

“Sit down, girl,” Linda patted the chair next to her, not next to Jacob. “While we wait for our appetizers, I have a few questions for you.”

An older lady smiling | Source: Midjourney

An older lady smiling | Source: Midjourney

I sank into the chair, still trying to make sense of this ambush. The waiter appeared with water glasses, and I found myself wishing it was something stronger.

That’s when Linda pulled out a crisp sheet of paper from her designer handbag.

“Now then,” she cleared her throat, clicking her gold-plated pen. “I’ve prepared a brief questionnaire to help us get to know you better. I want you to fill it out.”

Sheets of paper on a table | Source: Pexels

Sheets of paper on a table | Source: Pexels

My eyes scanned the paper she placed before me, each question worse than the last:

1. What is your current annual income and five-year career projection?

2. Please list any medical conditions, including a family history of genetic disorders.

3. How many romantic partners have you had, and what were the reasons for those relationships ending?

4. Do you own or lease your vehicle? What is your credit score?

5. Are you willing to sign a prenuptial agreement?

6. Do you plan to work after having children? If so, who will provide childcare?

7. What is your stance on living with in-laws?

8. Are you willing to host special occasions like Thanksgiving & Christmas every year without expecting a penny from your partner?

A startled woman covering her mouth | Source: Pexels

A startled woman covering her mouth | Source: Pexels

The questions went on and on like a never-ending train carriage. My water glass stopped halfway to my mouth. “I’m sorry, but is this for real?”

“Of course it is, dear,” Linda replied, her tone suggesting I was being deliberately difficult. “Our family has certain standards to maintain. We need to ensure any potential partners for our Jacob are… suitable.”

My eyes darted to Jacob, waiting for him to jump in, to say this was all a joke. But he just sat there, examining his napkin as if it held the secrets of the universe.

A man sitting casually | Source: Midjourney

A man sitting casually | Source: Midjourney

Something snapped inside me. Three months of building this connection, sharing hopes and fears, only to be treated like a job applicant? No. This called for a different approach.

“Would you excuse me for just a moment?” I smiled sweetly. “Ladies’ room.”

Instead of heading to the restroom, I ducked into the convenience store next door. Five minutes later, I returned with my own notebook and pen.

“Before I answer your questions,” I said, sitting down with renewed confidence, “I have a few of my own.”

A woman holding a piece of paper | Source: Pexels

A woman holding a piece of paper | Source: Pexels

Linda’s perfectly plucked eyebrows shot up in surprise as I placed the paper with my questions on the table. She picked it up and began reading loudly, her face speaking volumes of her anger.

“Question one: At what point did you realize your son wasn’t capable of choosing his own partner?”

Patricks’s face reddened. Jacob finally looked up from his napkin.

“Question two: How many women have actually completed your interrogation process? Or do most run screaming before the credit check?”

“This is completely inappropriate!” Linda’s voice pitched higher as she continued to read.

A furious older woman with a man | Source: Midjourney

A furious older woman with a man | Source: Midjourney

“Question three: Do you also inspect their teeth like show horses, or is that saved for the second date?”

“Question four: When Jacob moves out of your basement, will you be requiring his future wife to submit weekly progress reports?”

“Question five: Have you considered therapy for your control issues, or is that too personal a question?”

“That’s enough!” Jacob slammed his hand on the table, making the silverware jump. “You have no right to disrespect my family like this!”

An angry man | Source: Midjourney

An angry man | Source: Midjourney

I leaned back, crossing my arms. “Oh, but they have every right to treat me like I’m applying for a position at the FBI?”

“My parents are just looking out for me,” he protested, his voice weak. “They want what’s best— “

“No, Jacob. What’s best for you would be growing a backbone and living your own life.”

Linda and Patrick were already gathering their things, faces flushed with indignation. Linda’s hands shook as she stuffed her questionnaire back into her bag.

“We’re leaving,” she announced. “Jacob, come on. She’s not the one for you.”

“Wait!” I called out, loud enough for nearby tables to turn. “Aren’t you forgetting something?”

Side shot of a woman | Source: Midjourney

Side shot of a woman | Source: Midjourney

They paused. “WHAT??”

“Waiter, these people are trying to leave without paying their bill!” I announced loudly, waving to the waiter. “Guess running out on checks is another proud family tradition!”

The restaurant had gone quiet. Linda’s hands shook as she pulled out her credit card, practically throwing it at the waiter. I stood up, smoothing my dress once again.

“Well, this has been entertaining. I’ll cover my water.” I placed a five-dollar bill on the table and turned to Jacob.

“Good luck finding someone who meets your family’s rigorous standards. Although, you might want to try job recruitment sites instead of dating apps. I hear they provide detailed background checks and references.”

A woman laughing | Source: Midjourney

A woman laughing | Source: Midjourney

As I walked out into the cool evening air, my phone buzzed with a message from Jacob, “You didn’t have to be so cruel. My parents were just looking out for me.”

I typed back, “Just looking out for myself, mama’s boy. Goodbye!”

Later that night, Sarah called to hear about the date. After I finished telling her everything, she was quiet for a moment.

“You know what?” she finally said. “I bet Linda has a spreadsheet ranking all of Jacob’s potential wives.”

We both burst out laughing, and I felt the last of my disappointment melt away. Dodged a bullet? Absolutely. And I’ve never been so grateful for a red flag wrapped in a questionnaire.

A woman walking away | Source: Midjourney

A woman walking away | Source: Midjourney

This work is inspired by real events and people, but it has been fictionalized for creative purposes. Names, characters, and details have been changed to protect privacy and enhance the narrative. Any resemblance to actual persons, living or dead, or actual events is purely coincidental and not intended by the author.

The author and publisher make no claims to the accuracy of events or the portrayal of characters and are not liable for any misinterpretation. This story is provided “as is,” and any opinions expressed are those of the characters and do not reflect the views of the author or publisher.

Taylor Swift’s Chiefs Game Outfit Called ‘Cringe’ – Fans Say She Looks Like a Teen!

Taylor Swift’s outfit at the Kansas City Chiefs game has caused a lot of talk online.

On October 7, 2024, Taylor Swift made a big entrance at GEHA Field at Arrowhead Stadium to watch her boyfriend, Travis Kelce, play against the New Orleans Saints. Many were excited to see her, especially since she had missed two of his previous games. Her appearance was highly anticipated, and fans were eager to see what she would wear.

Her absence from earlier games sparked breakup rumors between her and Kelce. But by attending the game, she silenced those rumors and attracted a lot of attention from fans and photographers. Swift walked into the stadium wearing a short plaid dress and tall black boots.

Source: Getty Images

In a close-up photo, Swift’s slight smile and fresh look were highlighted. Her dress had an off-shoulder design, which showcased her gold jewelry nicely. In another picture, she smiled even more broadly, with her bangs framing her face. Her hair was pulled back in a casual ponytail, combining a glamorous and simple style.

One of the most talked-about parts of her look was the glittery freckles on her face, which sparkled under the stadium lights.

Source: Getty Images

Once her photos were shared online, people quickly voiced their opinions, which ranged from praise to criticism. One user joked, “I was wondering where my tablecloth [sic] went.” Another commenter criticized her boots, saying, “Bizarre boots!! They look awful on her.” Other comments included, “Is she dressed for football or a nightclub?” and “Grow up; she looks like a high school girl [sic].”

Source: Getty Images

Many comments focused on her footwear, with remarks like, “She can’t walk in those boots. So dumb…” But other fans defended her, saying, “She’s a wonderful human and so talented!” Another fan chimed in, “She’s awesome. She’s looking pretty niiice [sic].” One user who wasn’t a big fan of Swift added, “Not exactly a fan…but loving her outfit!”

Her facial glitter also caught attention. One fan commented, “The face glitter? Are you kidding? She’s so cute!” Another said, “Taylor Swift makes the whole place shimmer.”

Source: Getty Images

This isn’t the first time Swift has faced criticism for her outfits at Kelce’s games. Previously, on September 15, she attended a game wearing a red, oversized Kansas City Chiefs t-shirt as a mini dress, which fans labeled as “so trashy.” She paired it with thigh-high black leather boots, a black crossbody bag, and gold chains. Her signature hoop earrings and bold red lipstick completed her look, while her blonde hair fell in messy waves.

Source: Getty Images

Swift made a fashion statement as she arrived and later cheered from the Chiefs’ VIP suite. While some fans loved her bold style, others were not impressed. One user questioned, “With all her money, that’s what she wears?”

More negative comments followed, with one saying, “Omg… again her outfit is so trashy… what’s happening to her?” Another remarked, “Looking like an old-fashioned street walker as usual.” Critics also pointed out that her outfit seemed out of place compared to other players’ wives and girlfriends, who wore more traditional game-day clothing. One commenter said, “She dresses like a teenager.”

Source: Getty Images

Some wondered if her changing style was part of a strategy to gain publicity since her relationship with Kelce became public. “Her outfits are getting goofier. Does she really need the attention? Seems since Kelce, she’s all about PR,” wrote one user.

Source: Getty Images

Critics said her style didn’t fit with the more traditional game-day outfits worn by the wives and girlfriends of other players. One commenter said, “She dresses like a teenager.” Some even wondered if her changing style was a way to get more attention since her relationship with Kelce became public. One person wrote, “Her outfits are getting goofier. Does she really need the attention? Seems since Kelce she’s all about PR.”

This wasn’t the first time Swift’s outfit at a game had sparked criticism. Back on September 15, 2024, she wore a red oversized Kansas City Chiefs tee to a game between the Chiefs and the Cincinnati Bengals. Some fans didn’t like how she turned the tee into a mini dress.

She paired the look with thigh-high black leather boots, a black crossbody bag, and gold chains. Hoop earrings and her bold red lipstick completed the outfit, while her blonde hair was styled in messy waves. She later cheered from the Chiefs’ VIP suite.

Some fans didn’t like this outfit either. One user asked, “With all her money, that’s what she wears?” Another said, “Omg… again her outfit is so trashy… what’s happening to her?” Some even compared her look to that of an “old-fashioned street walker.”

Source: Getty Images

No matter what people think about her outfits, Swift continues to grab attention wherever she goes—on and off the football field.

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